My first experience with a crossdresser [M18, T25]

For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.

I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it.

My first experience with a crossdresser [M18, T25]

For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.

I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it.

My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times.